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LAST NIGHT, MINDY Kaling perfectly articulated one of my greatest fears. “I’m already stressed JT won’t play enough old songs at the super bowl,” she tweeted. Oh my God, Mindy, yes. I’ve never been more stressed about anything in my life.

This Sunday, Justin Timberlake will take to the stage in US Bank Stadium, Minneapolis, to perform one of the biggest shows of his life. Fourteen years after he inadvertently exposed Janet Jackson’s bare breast and permanently derailed her career, Timberlake is back to headline the Super Bowl halftime show.

The performance happens to coincide with the release of his fifth studio album, Man of the Woods, a project that has been greeted with shrugs and decidedly lukewarm reviews. In a one-minute teaser released at the beginning of the year, Timberlake pitched it as a personal album inspired by his family and where he’s from.

The accompanying visuals depicted Timberlake breathing in various landscapes and running purposefully through fields. The Mumford and Sons jokes came in thick and fast, as did speculation that Timberlake was about to do the unthinkable and release a country album.

A few days later, Timberlake appeared to upend expectations when he released Filthy, a futuristic, quintessentially Timberlakean jam produced by his longtime partners-in-crime Timbaland and Danja.

It elicited a Marmite response upon its release and failed to make an immediate impact, but it piqued this writer’s interest. After all, it didn’t sound like much else on the pop landscape. Perhaps this would herald the beginning of a new era for Timberlake.

Unfortunately, this optimism was short-lived. The next single was Supplies, a misfire in every conceivable way. The song represented an attempt to tap into the trap sound popularised by the likes of Migos. Instead it was reminiscent of your Dad doing an impression of Ali G about fifteen years after it was in vogue. Once again, the song hasn’t made much of an impression, save for countless articles decrying the video’s misjudged attempts at being woke.

Last week, we got more of an insight into the back-to-my-roots music Timberlake had promised when he released Say Something, a duet with country singer Chris Stapleton. It’s a rousing, irritatingly catchy country-pop song that manages to worm its way inside your head while remaining resolutely middle of the road.

The song’s central tenet? ‘Sometimes the greatest way to say something is to say nothing at all.’ Yes, quite. Nonetheless, the song has sat at number one on the US iTunes chart for the last week, a testament to both its crossover appeal and the enduring popularity of country music in the States.

The rest of the album was released today. It’s a messy hodgepodge of novelty Stetsons and Get Lucky B-sides. There are a few bright spots here and there, but it’s light years away from his best work. His last album, The 20/20 Experience, was similarly disappointing and bloated, yielding just one bona fide classic in the form of Mirrors.

It all begs the question: is Timberlake past it? Increasingly, it would seem so. Where Timberlake’s first two albums were daring and innovative, his latest efforts are lacklustre and, crucially, kind of uncool.

It doesn’t help that Timberlake briefly abandoned music to focus on an acting career that saw him star in the likes of The Social Network, Bad Teacher, Friends With Benefits and Inside Llewyn Davis, as well as countless Lonely Island sketches.

While he channeled his energy into becoming a leading man, he was usurped by the likes of The Weeknd and Bruno Mars, both of whom encroached on Timberlake’s territory as the heir apparent to Michael Jackson. The Weeknd had an irresistible falsetto and sultry bops like Can’t Feel My Face, Earned It and I Feel It Coming. Bruno Mars, meanwhile, was an all-round entertainer. He had the voice, he had the moves, and he had the hits. (How jealous do you think Timberlake was of Uptown Funk?)

Hell, even his longtime producer Pharrell swooped in when nobody was looking, lending his iconic falsetto to colossal hits like Get Lucky and Blurred Lines. He even had the bestselling song of 2014 with Happy.

Two years later, Justin Timberlake took a leaf from the Pharrell playbook and released Can’t Stop The Feeling, a song that cribs from Happy in just about every way imaginable. Both are kid-friendly pop songs recorded specifically for animated blockbusters and both videos are near duplicates of one another. It was a fairly brazen move on Timberlake’s part, but one that paid off in spades: it’s now among the biggest hits of his career.

There’s nothing on Man of the Woods that seems likely to replicate Can’t Stop The Feeling’s success, though. In fact, it seems like it might be time for Timberlake to accept that his best years are behind him.

There’s no shame in this. Timberlake has been active in the industry since N*Sync formed in 1995. He has a very impressive back catalogue – arguably the best of any male pop singer of the noughties. From pop classics like Cry Me A River and SexyBack to sweeping, swoony anthems like LoveStoned and Mirrors, he’s unrivaled. He remains a likeable, talented performer and consummate entertainer.

But the music industry is fickle and perhaps Timberlake shouldn’t strive for relevance by releasing bloated, indulgent pop albums that seem half-hearted at best. Instead, why not embrace his pop legacy and rest on his laurels for a bit? Shut up and play the hits, if you will.

A few weeks ago, Timberlake winced at the notion of a residency in Las Vegas, likening it to preparing for retirement. As his ex Britney Spears has proven, however, it can be a fruitful career move. Spears played in Las Vegas for four years. The show grossed $137.7 million and allowed Spears to reassert herself as a pop icon. She is now preparing to embark on a tour across the United States and Europe. (The Dublin date sold out in less than ten minutes.) Doesn’t sound like retirement to me.

On Sunday, Justin will play a fifteen-minute concert to hundreds of millions of viewers. Like many, I’ll be keeping my fingers crossed that he leaves the flannel shirt at home and gives the people what they want. The Justin that passes to the left and sails to the right.

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